JPH0759554B2 - カテコールカルボキサミド類 - Google Patents

カテコールカルボキサミド類

Info

Publication number: JPH0759554B2
Authority: JP; Japan
Prior art keywords: group; formula; compound; methyl; alkyl group
Prior art date: 1985-06-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP61503448A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63500239A (ja

Inventor

ハル，ホーカン・オロフ

ヒヨーグベルイ，トーマス

デパウリス，トーマス

ストリヨーム，ハンス・エリク・ペテル

オヨーグレン，スヴエン・ウーヴエ

Original Assignee

アストラ・レ−ケメデル・アクチエボラ−グ

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-06-19

Filing date

1986-06-12

Publication date

1995-06-28

1986-06-12 Application filed by アストラ・レ−ケメデル・アクチエボラ−グ filed Critical アストラ・レ−ケメデル・アクチエボラ−グ

1988-01-28 Publication of JPS63500239A publication Critical patent/JPS63500239A/ja

1995-06-28 Publication of JPH0759554B2 publication Critical patent/JPH0759554B2/ja

2010-06-28 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

QCIDBNKTKNBPKM-UHFFFAOYSA-N trencam-3,2-hopo Chemical class NC(=O)C1=CC=CC(O)=C1O QCIDBNKTKNBPKM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 100
125000000217 alkyl group Chemical group 0.000 claims abstract description 48
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 25
238000000034 method Methods 0.000 claims abstract description 22
125000002252 acyl group Chemical group 0.000 claims abstract description 14
125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 12
125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
230000003287 optical effect Effects 0.000 claims abstract description 11
125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 51
-1 methylenedioxy Chemical group 0.000 claims description 34
239000000460 chlorine Substances 0.000 claims description 24
238000009472 formulation Methods 0.000 claims description 17
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
125000001246 bromo group Chemical group Br* 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
150000001408 amides Chemical group 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 4
239000012039 electrophile Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
239000002552 dosage form Substances 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
208000020016 psychiatric disease Diseases 0.000 claims description 2
229910052710 silicon Inorganic materials 0.000 claims description 2
239000000543 intermediate Substances 0.000 abstract description 6
230000001225 therapeutic effect Effects 0.000 abstract description 3
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 abstract 1
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 69
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 28
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 28
239000013543 active substance Substances 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
229960003638 dopamine Drugs 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 15
229960004046 apomorphine Drugs 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
238000000921 elemental analysis Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000003826 tablet Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
239000002904 solvent Substances 0.000 description 10
102000005962 receptors Human genes 0.000 description 9
108020003175 receptors Proteins 0.000 description 9
229910004298 SiO 2 Inorganic materials 0.000 description 8
239000002253 acid Substances 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000002775 capsule Substances 0.000 description 8
239000003480 eluent Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000700159 Rattus Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
239000007903 gelatin capsule Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
239000002585 base Substances 0.000 description 6
210000004720 cerebrum Anatomy 0.000 description 6
229920000159 gelatin Polymers 0.000 description 6
235000019322 gelatine Nutrition 0.000 description 6
208000013403 hyperactivity Diseases 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
208000011580 syndromic disease Diseases 0.000 description 6
238000012360 testing method Methods 0.000 description 6
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
206010042008 Stereotypy Diseases 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000008273 gelatin Substances 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
229950001675 spiperone Drugs 0.000 description 5
239000008107 starch Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
AOLAYIKZZRFLAN-UHFFFAOYSA-N 5-bromo-2,3-dimethoxybenzoyl chloride Chemical compound COC1=CC(Br)=CC(C(Cl)=O)=C1OC AOLAYIKZZRFLAN-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
208000028017 Psychotic disease Diseases 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000000561 anti-psychotic effect Effects 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
230000000903 blocking effect Effects 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
102000015554 Dopamine receptor Human genes 0.000 description 3
108050004812 Dopamine receptor Proteins 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000000164 antipsychotic agent Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003176 neuroleptic agent Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
201000000980 schizophrenia Diseases 0.000 description 3
238000000926 separation method Methods 0.000 description 3
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 3
GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
ZKMWQUDSDYOEJQ-UHFFFAOYSA-N 5-bromo-2,3-dimethoxybenzoic acid Chemical compound COC1=CC(Br)=CC(C(O)=O)=C1OC ZKMWQUDSDYOEJQ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
208000020401 Depressive disease Diseases 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
206010047700 Vomiting Diseases 0.000 description 2
UNRBEYYLYRXYCG-ZETCQYMHSA-N [(2s)-1-ethylpyrrolidin-2-yl]methanamine Chemical compound CCN1CCC[C@H]1CN UNRBEYYLYRXYCG-ZETCQYMHSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
208000028505 alcohol-related disease Diseases 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
230000003474 anti-emetic effect Effects 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000006399 behavior Effects 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
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230000002490 cerebral effect Effects 0.000 description 2
230000008859 change Effects 0.000 description 2
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238000001816 cooling Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
230000001054 cortical effect Effects 0.000 description 2
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
239000011968 lewis acid catalyst Substances 0.000 description 2
230000002197 limbic effect Effects 0.000 description 2
230000033001 locomotion Effects 0.000 description 2
GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluenecarboxylic acid Natural products CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
239000012528 membrane Substances 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000000312 peanut oil Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000004044 response Effects 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
208000019116 sleep disease Diseases 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
238000013222 sprague-dawley male rat Methods 0.000 description 2
230000002739 subcortical effect Effects 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
230000008673 vomiting Effects 0.000 description 2
238000005303 weighing Methods 0.000 description 2
ZZJYIKPMDIWRSN-TZBSWOFLSA-N (+)-butaclamol Chemical compound C12=CC=CC=C2CCC2=CC=CC3=C2[C@@H]1CN1CC[C@@](C(C)(C)C)(O)C[C@@H]13 ZZJYIKPMDIWRSN-TZBSWOFLSA-N 0.000 description 1
OEYAFMGVIFWPQI-UHFFFAOYSA-N (1-benzylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1CC1=CC=CC=C1 OEYAFMGVIFWPQI-UHFFFAOYSA-N 0.000 description 1
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VJKBFGZFBOADLG-ZDUSSCGKSA-N n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-2,3-dimethoxy-5-methylbenzenecarbothioamide Chemical compound CCN1CCC[C@H]1CNC(=S)C1=CC(C)=CC(OC)=C1OC VJKBFGZFBOADLG-ZDUSSCGKSA-N 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
210000001009 nucleus accumben Anatomy 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
229960001779 pargyline Drugs 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 description 1
238000011552 rat model Methods 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008227 sterile water for injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000007939 sustained release tablet Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Compounds Of Unknown Constitution (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP61503448A 1985-06-19 1986-06-12 カテコールカルボキサミド類 Expired - Lifetime JPH0759554B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE8503054A SE8503054D0 (sv)	1985-06-19	1985-06-19	Catecholcarboxamides
SE8503054-2		1985-06-19
PCT/SE1986/000283 WO1986007591A1 (en)	1985-06-19	1986-06-12	Catecholcarboxamides, process for their preparation, intermediates and a pharmaceutical preparation

Publications (2)

Publication Number	Publication Date
JPS63500239A JPS63500239A (ja)	1988-01-28
JPH0759554B2 true JPH0759554B2 (ja)	1995-06-28

Family

ID=20360638

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61503448A Expired - Lifetime JPH0759554B2 (ja)	1985-06-19	1986-06-12	カテコールカルボキサミド類

Country Status (6)

Country	Link
EP (1)	EP0207913B1 (de)
JP (1)	JPH0759554B2 (de)
AT (1)	ATE57913T1 (de)
DE (1)	DE3675277D1 (de)
SE (1)	SE8503054D0 (de)
WO (1)	WO1986007591A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI95572C (fi) *	1987-06-22	1996-02-26	Eisai Co Ltd	Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi
US5122361A (en) *	1989-04-17	1992-06-16	Trustees Of The University Of Pennsylvania	Dopamine receptor ligands and imaging agents
US5186921A (en) *	1989-04-17	1993-02-16	Trustees Of The University Of Pennsylvania	Dopamine receptor ligands and image agents
US5446147A (en) *	1992-04-03	1995-08-29	Trustees Of The University Of Pennsylvania	Fluorinated and iodinated dopamine agents

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3342826A (en) *	1964-01-13	1967-09-19	Ile De France	Heterocyclic aminoalkyl benzamides
JPS50123668A (de) *	1974-03-05	1975-09-29	Soc Et Scient Et Ind
DE3334594A1 (de) *	1983-09-24	1985-04-04	Boehringer Ingelheim KG, 6507 Ingelheim	Basisch substituierte 2,4-dimethoxybenzamide, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu ihrer herstellung

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR5916M (de) *	1966-01-21	1968-05-06
CH605793A5 (fr) *	1974-03-05	1978-10-13	Soc Et Scient Et Ind	Procédé de préparation de nouveaux N-(1benzylpyrrollidinil 2-alkyl) benzamides substitués
SE411118B (sv) *	1978-03-23	1979-12-03	Astra Laekemedel Ab	Ett forfarande for framstellning av 2,6-dialkoxibensamider med terapentiska egenskaper
JPS57149532A (en) *	1981-03-06	1982-09-16	Tsudakoma Ind Co Ltd	Weft yarn storing apparatus for fluid jet type loom
SE8101536L (sv) *	1981-03-11	1982-09-12	Astra Laekemedel Ab	Bensamid-derivat
US4470977A (en) *	1981-06-04	1984-09-11	Adria Laboratories, Inc.	Antiemetic and antipsychotic agents

1985
- 1985-06-19 SE SE8503054A patent/SE8503054D0/xx unknown
1986
- 1986-06-12 WO PCT/SE1986/000283 patent/WO1986007591A1/en not_active Ceased
- 1986-06-12 EP EP86850209A patent/EP0207913B1/de not_active Expired - Lifetime
- 1986-06-12 DE DE8686850209T patent/DE3675277D1/de not_active Expired - Fee Related
- 1986-06-12 AT AT86850209T patent/ATE57913T1/de not_active IP Right Cessation
- 1986-06-12 JP JP61503448A patent/JPH0759554B2/ja not_active Expired - Lifetime

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3342826A (en) *	1964-01-13	1967-09-19	Ile De France	Heterocyclic aminoalkyl benzamides
JPS50123668A (de) *	1974-03-05	1975-09-29	Soc Et Scient Et Ind
DE3334594A1 (de) *	1983-09-24	1985-04-04	Boehringer Ingelheim KG, 6507 Ingelheim	Basisch substituierte 2,4-dimethoxybenzamide, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu ihrer herstellung

Also Published As

Publication number	Publication date
ATE57913T1 (de)	1990-11-15
WO1986007591A1 (en)	1986-12-31
EP0207913B1 (de)	1990-10-31
SE8503054D0 (sv)	1985-06-19
EP0207913A1 (de)	1987-01-07
DE3675277D1 (de)	1990-12-06
JPS63500239A (ja)	1988-01-28

Publication	Publication Date	Title
JPH07165749A (ja)	1995-06-27	三環式芳香族化合物
KR890001375B1 (ko)	1989-05-02	벤즈아미도 유도체의 제조 방법
US4299831A (en)	1981-11-10	2-Trifluoromethyl-3-quinoline carboxamides, analgesic and anti-inflammatory compositions and methods employing them
KR890004196B1 (ko)	1989-10-27	신규 벤조티아진 유도체의 제조방법
HU184712B (en)	1984-10-29	Process for producing dextrorotating trans-2-substituted-5-phenyl-2,3,4,4a,5,9b,hexahydro-h-pyrido-bracket-4,3,b-bracket closedindol derivatives
KR900008316B1 (ko)	1990-11-12	벤즈아미도 유도체의 제조방법
JPH09512542A (ja)	1997-12-16	Ｄ▲下４▼リセプタ拮抗剤としてのベンゾフラン誘導体
HU202226B (en)	1991-02-28	Process for producing tetrazol derivatives and pharmaceutical compositions containing them
GB2176785A (en)	1987-01-07	Annellated benzamide derivatives
HU177793B (en)	1981-12-28	Process for producing 2,6-dialkoxy-benzamides
KR900006743B1 (ko)	1990-09-20	천식치료제인 치환된 테트랄린, 크로만 및 관련화합물
JPH0759554B2 (ja)	1995-06-28	カテコールカルボキサミド類
CN1043574C (zh)	1999-06-09	具有中枢神经系统活性的杂环胺
JPS62185075A (ja)	1987-08-13	インデノ〔１，７−ｃｄ〕アゼピン類
JPH04193867A (ja)	1992-07-13	イソキノリノール誘導体及び医薬
EP0175452B1 (de)	1988-09-21	1,3-Disubstituierte Piperidinverbindungen als neuroleptische Mittel
US4623728A (en)	1986-11-18	Intermediates for 1,3-disubstituted piperidine compounds as neuroleptic agents
JPH0559117B2 (de)	1993-08-30
JPH0780888B2 (ja)	1995-08-30	ピロロ〔１，２−ａ〕〔４，１〕ベンゾオキサゼピン誘導体
IE67871B1 (en)	1996-05-01	Novel benzothiopyranylamines
JP2733490B2 (ja)	1998-03-30	置換１，３，４，９‐テトラヒドロピラノ［３，４‐ｂ］インドール‐１‐酢酸
CA2346506C (fr)	2009-01-13	Derives d'aryl-{4-fluoro-4-[(2-pyridin-2-yl-ethylamino)-methyl]-piperidin-1-yl}-methanone comme agonistes du recepteur 5-ht1
JP2740296B2 (ja)	1998-04-15	アルコキシチオフェンカルボキシアミド誘導体、その製造方法及び該化合物を含有する医薬組成物
US5240957A (en)	1993-08-31	Oxysalicylamido derivatives
JPH07103097B2 (ja)	1995-11-08	オキシサリチルアミド誘導体